4-((4-methoxyphenyl)amino)butanenitrile | 855621-17-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-((4-methoxyphenyl)amino)butanenitrile
• 英文别名: 4-(4-Methoxyanilino)butanenitrile
• CAS: 855621-17-9
• 化学式: C₁₁H₁₄N₂O
• mdl: MFCD11154355
• 分子量: 190.245
• InChiKey: UXRITVSMIMZKMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  45
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-((4-methoxyphenyl)amino)butanenitrile 在 硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以81%的产率得到N-(4-methoxyphenyl)tetramethylenediamine
  参考文献：
  名称：

  An Efficient Synthesis of N-Arylputrescines and Cadaverines

  摘要：

  我们介绍了一种通过碳酸铯介导的苯胺与Ï-氯腈的烷基化反应以及随后的还原反应，分两步合成 N-芳基putrescines 和adaverines 的通用方法。铯介导的烷基化反应对单烷基化产物具有显著的选择性。该方法简便易行，并能获得令人满意的总产率。

  DOI：

  10.1055/s-0028-1087817
• 作为产物：
  描述：

  丙烯腈 、 N-(4-甲氧基苯基)甲亚胺 在 1,10-邻菲啰啉二溴化镍 、 水 、 锌 作用下， 以 乙腈 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 20.0h， 以63%的产率得到4-((4-methoxyphenyl)amino)butanenitrile
  参考文献：
  名称：

  通过镍催化的醛亚胺和活化烯烃的还原偶联，γ-氨基酯，腈，砜和吡咯烷酮的区域选择性合成。

  摘要：

  DOI：

  10.1002/anie.200800825

文献信息

• Copper-Catalyzed Cyanoalkylation of Amines via C–C Bond Cleavage: An Approach for C(sp³)–N Bond Formations
  作者：Lin Yang、Jia-Yu Zhang、Xin-Hua Duan、Pin Gao、Jiao Jiao、Li-Na Guo

  DOI：10.1021/acs.joc.9b01084

  日期：2019.7.5

  The efficient copper-catalyzed cyanoalkylation of amines via C–C bond cleavage has been demonstrated. Distinctive features of this procedure involves mild conditions, broad range of nitrogen nucleophiles, high selectivity, and good functional group tolerance, thus providing a useful approach for the C(sp3)–N bond formations. Most importantly, this protocol is applicable to the late-stage functionalization

  已经证明了通过C–C键裂解的铜的高效胺催化氰基烷基化反应。此过程的显着特征涉及温和条件，宽范围的氮亲核试剂，高选择性和良好的官能团耐受性，因此为形成C（sp 3）–N键提供了一种有用的方法。最重要的是，该协议适用于天然产物，氨基酸酯和药物的后期功能化。机理研究表明，自由基中间体参与了这一转变。
• Synthesis of 1,6-Disubstituted 4,5,6,7-Tetrahydropyrazolo[3,4-c]pyridin-7-one Derivatives and Evaluation of Their Anticancer Activity
  作者：Vani Nelamane Devegowda、Seon-Hee Seo、Ae Nim Pae、Ghil-Soo Nam、Kyung-Il Choi

  DOI：10.5012/bkcs.2012.33.2.647

  日期：2012.2.20

  Promising anticancer compounds of the type 1,6-disubstituted 4,5,6,7-tetrahydropyrazolo[3,4-c]pyridin-7-ones were identified. The target compounds were readily synthesized in a large scale via a sequence of reactions starting from the commercially available primary amines. Their in vitro anti-proliferative activity has been evaluated on prostate (DU-145), colon (HT-29 and HCT-116) and melanoma (A375P) human cancer cell lines. The relationships between the structure and the anticancer activity, covering all tested cancer cell lines, revealed that the compound 5c with 2,4-dimethylphenyl substituent at $R^2$ was the most potent with the $IC_50}$ values in the range as low as 0.16 to $0.40\mu}M$.

  发现了有前景的抗癌化合物，类型为1,6-二取代的4,5,6,7-四氢吡咯并[3,4-c]吡啶-7-酮。这些靶化合物通过一系列反应，从商业可获得的初级胺出发，容易大规模合成。它们在前列腺（DU-145）、结肠（HT-29和HCT-116）以及黑色素瘤（A375P）的人癌细胞系上进行了体外抗增殖活性评估。结构与抗癌活性之间的关系覆盖了所有测试的癌细胞系，结果显示，化合物5c在处具有2,4-二甲基苯取代基，是最有效的，其值低至0.16至<0.40\mu}M>。
• NOVEL 1,6-DISUBSTITUTED-3-AMINO-4,5,6,7-TETRAHYDRO-1H-PYRAZOLO[3,4-C]PYRIDIN-7-ONE COMPOUNDS AND PREPARATION THEREOF
  申请人：NAM Ghilsoo

  公开号：US20110319619A1

  公开（公告）日：2011-12-29

  Provided are a novel 1,6-disubstituted-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridin-7-one compound, a pharmaceutically acceptable salt compound thereof, a method for preparing the compound, and an anticancer pharmaceutical composition including the compound as an effective ingredient.

  提供了一种新颖的1,6-二取代-4,5,6,7-四氢-1H-吡唑并[3,4-c]吡啶-7-酮化合物，其药用盐化合物，一种制备该化合物的方法，以及包含该化合物作为有效成分的抗癌药物组合物。
• Single-Electron-Transfer-Induced C(sp³)–N Couplings via C–C Bond Cleavage of Cycloketoxime Esters
  作者：Binlin Zhao、Minyan Wang、Zhuangzhi Shi

  DOI：10.1021/acs.joc.9b01338

  日期：2019.8.16

  A practical single-electron-transfer-induced selective C(sp(3))-N coupling of cycloketoximes with anilines via C-C bond cleavage under copper-catalytic and synergetic photoredox/copper-catalytic reaction systems has been uncovered. These two powerful and simple protocols demonstrated excellent selectivity and good functional group compatibility without any base or ligand control. Preliminary mechanistic experiments indicated that a radical-mediated process was involved in these transformations.
• Synthesis and the 5-HT6 receptor antagonistic effect of 3-arylsulfonylamino-5,6-dihydro-6-substituted pyrazolo[3,4]pyridinones for neuropathic pain treatment
  作者：Vani Nelamane Devegowda、Jin-Ri Hong、Sungjin Cho、Eun Jeong Lim、Hyunah Choo、Gyochang Keum、Hyewon Rhim、Ghilsoo Nam

  DOI：10.1016/j.bmcl.2013.05.100

  日期：2013.8

  A novel series of 3-arylsulfonylamino-5,6-dihydro-6-substituted-1H-pyrazolo[3,4-c]pyridine-7-ones was designed and synthesized as 5-HT6 ligands. Among the derivatives synthesized, the lead compound, 12b, having piperidine functionality at the 6-position and (1-naphthyl)sulfonamino at the 3-position of the core structure showed the most potent 5-HT6 inhibitory activity in vitro, good stability without CYP liability, and good neuropathic pain alleviation activity in a rat animal model. (C) 2013 Elsevier Ltd. All rights reserved.